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EP2773721B1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
EP2773721B1
EP2773721B1 EP12775140.2A EP12775140A EP2773721B1 EP 2773721 B1 EP2773721 B1 EP 2773721B1 EP 12775140 A EP12775140 A EP 12775140A EP 2773721 B1 EP2773721 B1 EP 2773721B1
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Prior art keywords
group
aromatic
radicals
atoms
substituted
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EP12775140.2A
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German (de)
English (en)
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EP2773721A1 (fr
Inventor
Amir Hossain Parham
Christof Pflumm
Anja JATSCH
Thomas Eberle
Philipp Stoessel
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Merck Patent GmbH
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Merck Patent GmbH
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to electronic devices, in particular organic electroluminescent devices, materials for use in electronic devices, in particular in organic electroluminescent devices, and a method for producing these materials.
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • the emissive materials increasingly used are organometallic complexes which exhibit phosphorescence instead of fluorescence.
  • organometallic compounds as phosphorescence emitters.
  • OLEDs organic electroluminescent devices
  • the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
  • the other materials used such as matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials are of particular importance. Improvements to these materials can thus also lead to significant improvements in the OLED properties. Even for fluorescent OLEDs there is still room for improvement with these materials.
  • ketones for example according to US Pat WO 2004/093207 or WO 2010/006680 .
  • matrix materials for example according to US Pat WO 2004/093207 or WO 2010/006680 .
  • using these matrix materials as well as other matrix materials there is still room for improvement, especially with regard to the efficiency and the lifetime of the device.
  • the object of the present invention is to provide compounds which are suitable for use in a fluorescent or phosphorescent OLED, in particular a phosphorescent OLED, for example as matrix material or as hole transport / electron blocking material or exciton blocking material or as electron transport or hole blocking material.
  • a fluorescent or phosphorescent OLED in particular a phosphorescent OLED
  • matrix material for example as matrix material or as hole transport / electron blocking material or exciton blocking material or as electron transport or hole blocking material.
  • An electronic device in the sense of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component may also contain inorganic materials or even layers which are completely composed of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells (O-DSSC), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-laser) and "organic plasmon emitting devices” ( Koller et al., Nature Photonics 2008, 1-4 ), preferably organic electroluminescent devices (OLEDs) and particularly preferably phosphorescent OLEDs.
  • OLEDs organic electroluminescent devices
  • O-ICs organic integrated circuits
  • O-FETs organic field-effect transistors
  • OF-TFTs organic thin-film transistors
  • An aryl group in the sense of this invention contains 6 to 60 C atoms;
  • a heteroaryl group contains 2 to 60 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • an aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline , etc., understood.
  • aromatics linked to one another by single bond such as, for example, biphenyl, are not designated as aryl or heteroaryl group but as aromatic ring system.
  • An aromatic ring system in the sense of this invention contains 6 to 80 carbon atoms in the ring system.
  • a heteroaromatic ring system in the sense of this invention contains 2 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups a non-aromatic moiety, such as As a C, N or O atom can be connected.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example are linked by a short alkyl group.
  • An aryl or heteroaryl group with not more than two directly condensed aromatic six-membered rings are understood as meaning simple aryl or heteroaryl groups, for example benzene or pyridine, or aryl or heteroaryl groups having exactly two aromatic six-membered rings condensed together, for example naphthalene or quinoline , Furthermore, these are understood to mean heteroaryl groups in which aromatic five-membered rings and six-membered rings, but non-aromatic six-membered rings, are directly fused to one another, such as, for example, carbazole, dibenzofuran, dibenzothiophene or benzimidazole.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 40 C atoms, and in which also individual H atoms or CH 2 groups, may be represented by the abovementioned groups
  • the radicals are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl , Cyclopentyl, n-hexyl, neo -hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroeth radical or n-propyl,
  • alkoxy group having 1 to 40 carbon atoms methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
  • alkyl, alkoxy or thioalkyl groups according to the present invention may be straight-chain, branched or cyclic, wherein one or more non-adjacent CH 2 groups may be replaced by the above-mentioned groups;
  • one or more H atoms can also be replaced by D, F, Cl, Br, I, CN or NO 2 , preferably F, Cl or CN, more preferably F or CN, particularly preferably CN.
  • aromatic or heteroaromatic ring system with 5-60 aromatic ring atoms which may be substituted in each case with the above-mentioned radicals R 2 or a hydrocarbon radical and which via any position on the aromatic or heteroaromatic
  • groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, benzanthracene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene are meant , Dihydropyrenes, tetrahydropyrenes, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolo-carbazole, Truxen
  • adjacent radicals R or "R 1" is understood to mean radicals which bind to carbon atoms which are bonded directly to one another or radicals which bind to the same carbon atom.
  • Ar is more preferably identical or different at each occurrence selected from the group consisting of benzene, pyridine, thiophene, furan, pyrrole, carbazole, fluorene, benzofuran, benzothiophene, dibenzofuran or dibenzothiophene, which may each be substituted by one or more R radicals.
  • Ar on each occurrence is benzene, which may be substituted by one or more radicals R, thus very particularly preferably represents a group of formula (2) or formula (6), in each of which all groups X are CR ,
  • both Ar groups are the same aryl or heteroaryl group.
  • the two groups Ar may be the same or different substituted.
  • Preferred embodiments of the compounds of formula (1) are the compounds of the following formulas (11) to (21), wherein the symbols used have the meanings given above.
  • At most one group X per cycle stands for N and the other groups X stand the same or different for each occurrence of CR. In a particularly preferred embodiment of the invention, all groups X are the same or different at each occurrence for CR.
  • Ar 1 represents an aromatic or heteroaromatic ring system having from 5 to 24 aromatic ring atoms which may be substituted by one or more Rs and which does not contain aryl or heteroaryl groups having more than two directly fused aromatic six-membered rings.
  • Ar 1 and also the radicals R bound to Ar 1 preferably contain no aromatic six-membered rings condensed directly together.
  • Particularly preferred groups Ar 1 are selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho, meta, para or branched terphenyl, linear or branched quaterphenyl, fluorene, in particular 2-fluorene, spirobifluorene, in particular 2-spirobifluorene, carbazole, in particular 2- or 3-carbazole, dibenzothiophene, in particular 1-, 2- or 3-dibenzothiophene, dibenzofuran, in particular 1-, 2- or 3-dibenzofuran, 1,3,5-triazine, pyridine , Pyrimidine, indenocarbazole, bridged carbazole or indolocarbazole or combinations of two or three of these groups. These groups may each be substituted by one or more radicals R.
  • the index n 0.
  • This preference also applies to the abovementioned compounds of the formula (12) or (12a) to (12d).
  • orientation shown in structure (A) in which one carbonyl group and one group NAr 1 are bonded to each group Ar is the preferred orientation.
  • the group Ar 1 is preferably selected from the groups Ar 1 mentioned above as preferred.
  • the two groups Ar 1 are particularly preferably chosen to be the same in the molecule.
  • R in the above formulas is the same or different at each occurrence selected from the group consisting of H, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which may be substituted by one or more R 2 , or an aromatic or heteroaromatic Ring system having 5 to 18 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals.
  • R is an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 .
  • R is an aromatic or heteroaromatic ring system, it preferably contains no aryl or heteroaryl groups in which more than two aromatic six-membered rings are directly fused to each other, and most preferably does not contain any aryl or heteroaryl groups in which aromatic six-membered rings directly condense to one another are.
  • R as a substituent on the groups Ar is an aromatic or heteroaromatic ring system, this is particularly preferably selected from the group consisting of benzene, ortho, meta or para biphenyl, ortho, meta, para or branched terphenyl , linear or branched quaterphenyl, fluorene, in particular 2-fluorene, spirobifluorene, in particular 2-spirobifluorene, carbazole, in particular 2- or 3-carbazole or N-carbazole, dibenzothiophene, in particular 1-, 2- or 3-dibenzothiophene, dibenzofuran, in particular 1-, 2- or 3-dibenzofuran, 1,3,5-triazine, pyridine, pyrimidine or combinations of two or three of these groups. These groups may each be substituted by one or more radicals R 2 .
  • the alkyl groups preferably have not more than five carbon atoms, more preferably not more than 4 carbon atoms, most preferably not more than 1 carbon atom.
  • Examples of preferred compounds according to the above-mentioned embodiments are the compounds of the following structures (1) to (201). (1) (2) (3) (4) (5) (6) (7) (8th) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35.) (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) (47) (48) (49) (50) (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (76) (77) (78) (79) (80) (81) (82) (83) (84) (85) (86) (87) (88) (89) (90) (91) (92) (93) (94) (95) (96) (97) (98) (99) (
  • the organic electroluminescent device includes cathode, anode and at least one emitting layer. In addition to these layers, they may also contain further layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, Exciton blocking layers, electron blocking layers and / or charge generation layers (charge generation layers). Likewise, interlayer may be introduced between two emitting layers which, for example, have an exciton-blocking function. It should be noted, however, that not necessarily each of these layers must be present. In this case, the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers.
  • emission layers are present, they preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie in the emitting layers different emitting compounds are used, which can fluoresce or phosphoresce.
  • white emission can be preferentially generated by using a blue emission layer and an emission layer emitting red and green, and these two emission layers can be separated from each other by a charge generation layer.
  • the compound according to formula (1) can be used in different layers, depending on the exact structure. Preference is given to an organic electroluminescent device comprising a compound according to formula (1) or the preferred embodiments described above as matrix material for fluorescent or phosphorescent emitters, in particular for phosphorescent emitters, and / or in a hole blocking layer and / or in an electron transport layer and / or in an electron-blocking or exciton-blocking layer and / or in a hole transport layer, depending on the exact substitution.
  • the organic electroluminescent device contains the compound according to formula (1) or the above-described preferred embodiments in an optical coupling-out layer.
  • An optical coupling-out layer is understood to be a layer which does not lie between the anode and the Cathode is located, but the outside of the actual device is applied to an electrode, for example, between an electrode and a substrate in order to improve the optical outcoupling.
  • the compound according to formula (1) or the above-described preferred embodiments is used as matrix material for a fluorescent or phosphorescent compound, in particular for a phosphorescent compound, in an emitting layer.
  • the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers, wherein at least one emitting layer contains at least one compound according to formula (1) as matrix material.
  • the compound according to formula (1) or the preferred embodiments outlined above is used as the matrix material for an emitting compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
  • Phosphorescence in the sense of this invention is understood to mean the luminescence from an excited state with a spin multiplicity> 1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • the mixture of the compound according to formula (1) or the above-described preferred embodiments and the emitting compound contains between 99 and 1 vol.%, Preferably between 98 and 10 vol.%, Particularly preferably between 97 and 60 vol. %, in particular between 95 and 80 vol .-% of the compound according to formula (1) or the above-described preferred embodiments based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, more preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter relative to the total mixture made of emitter and matrix material. Depending on the choice of the matrix material and a lower emitter concentration may be preferred, such as. B. in the application not disclosed EP 11002816.4 described.
  • a further preferred embodiment of the present invention is the use of the compound of the formula (1) or of the above-described preferred embodiments as a matrix material for a phosphorescent emitter in combination with another matrix material.
  • a further preferred embodiment of the present invention is the use of the compound according to formula (1) or according to the preferred embodiments as a matrix material for a phosphorescent emitter in combination with another matrix material.
  • Particularly suitable matrix materials which can be used in combination with the compounds according to formula (1) or according to the preferred embodiments are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, eg. B. according to WO 2004/013080 . WO 2004/093207 .
  • WO 2006/005627 or WO 2010/006680 Triarylamines, carbazole derivatives, e.g. B. CBP (N, N-bis-carbazolylbiphenyl) or in WO 2005/039246 . US 2005/0069729 . JP 2004/288381 .
  • EP 1205527 or WO 2008/086851 disclosed carbazole derivatives, indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746 , Indenocarbazole derivatives, e.g. B. according to WO 2010/136109 .
  • Diazasilol- or tetraazasilol derivatives z. B. according to WO 2010/054729
  • Diazaphosphole derivatives e.g. B. according to WO 2010/054730 bridged carbazole derivatives, e.g. B. according to US 2009/0136779 .
  • WO 2010/050778 WO 2011/042107 .
  • WO 2011/088877 or according to the application not disclosed EP 11003232.3
  • Triphenylenderivaten z. B. according to the application not disclosed DE 102010048608.6
  • lactams e.g. B. according to the applications not disclosed DE 102010012738.8 or DE 102010019306.2
  • a further phosphorescent emitter which emits shorter wavelength than the actual emitter, may be present as a co-host in the mixture.
  • Suitable phosphorescent compounds are, in particular, compounds which emit light, preferably in the visible range, with suitable excitation and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number.
  • Preferred phosphorescence emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium, platinum or copper.
  • the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, ie the emitting layer directly adjoins the hole injection layer or the anode, and / or the emitting layer directly adjoins the electron transport layer or the electron injection layer or the cathode, such as in WO 2005/053051 described.
  • a metal complex which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport or to use hole injection material, such as. In WO 2009/030981 described.
  • the compound according to formula (1) or the above-described preferred embodiments is used as an electron transport material in an electron transport or electron injection layer.
  • the emitting layer may be fluorescent or phosphorescent.
  • the compound when used as an electron transport material, it may be preferred if it is doped, for example, with alkali metal complexes, such as. B. LiQ (Lithiumhydroxychinolinat).
  • the compound according to formula (1) or the above-described preferred embodiments is used in a hole blocking layer.
  • a hole blocking layer is understood as meaning a layer which directly adjoins an emitting layer on the cathode side.
  • the compound according to formula (1) or the above-described preferred embodiments is used in a hole transport layer or in an electron blocking layer or exciton blocking layer.
  • an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process.
  • the materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. But it is also possible that the initial pressure is even lower, for example less than 10 -7 mbar.
  • an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
  • the materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • OVJP Organic Vapor Jet Printing
  • the materials are applied directly through a nozzle and thus structured (eg. MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301 ).
  • an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
  • any printing process such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (ink jet printing) or Nozzle Printing, are produced.
  • soluble compounds are necessary, which are obtained for example by suitable substitution. These methods are particularly suitable for oligomers, dendrimers and polymers.
  • hybrid processes are possible in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.
  • both synthetic methods can be carried out both on the amine, which is then oxidized in a subsequent step to the lactam, as shown in Scheme 2, or they can be carried out on the amide, as shown in Scheme 3.
  • both reaction types very good yields are obtained in the ring closure reaction.
  • Another object of the present invention is the use of the compounds of the invention according to formula (1 ') in an electronic device, in particular in an organic electroluminescent device.
  • the educts can from the companies ALDRICH or ABCR (palladium (II) acetate, tri-o-tolylphosphine, inorganics, solvents).
  • ALDRICH aluminum (II) acetate, tri-o-tolylphosphine, inorganics, solvents).
  • the data for the educts known from the literature are the CAS numbers.
  • Example 17 10- (2-bromobenzyl) -9,9-dimethyl-9,10-dihydro-acridine
  • inventive OLEDs and OLEDs according to the prior art is carried out according to a general method according to WO 2004/058911 , which is adapted to the conditions described here (layer thickness variation, materials).
  • the OLEDs have the following layer structure: substrate / optional hole injection layer (HIL) / hole transport layer (HTL) / Optional Interlayer (IL) / Electron Blocker Layer (EBL) / Emission Layer (EML) / Optional Hole Blocking Layer (HBL) / Electron Transport Layer (ETL) / Optional Electron Injection Layer (EIL) and finally a cathode.
  • the cathode is formed by a 100 nm thick aluminum layer.
  • Table 1 A designation such as "3f” refers to the compound of Example 3f, etc.
  • the other materials needed to make the OLEDs are shown in Table 3.
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material or the matrix materials by co-evaporation in a specific volume fraction.
  • the electron transport layer may consist of a mixture of two materials.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra are determined at a luminance of 1000 cd / m 2 and from this the CIE 1931 x and y color coordinates are calculated.
  • the indication U1000 in Table 2 indicates the voltage required for a luminance of 1000 cd / m 2 .
  • SE1000 and LE1000 indicate the power efficiency achieved at 1000 cd / m 2 .
  • EQE1000 refers to external quantum efficiency at an operating luminance of 1000 cd / m 2 .
  • Examples V1 and V2 are comparative examples according to the prior art Technique
  • Examples E1-E19 show data of OLEDs with materials according to the invention.

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Claims (13)

  1. Dispositif électronique comprenant un composé de la formule (1) :
    Figure imgb0497
     dans laquelle ce qui suit s'applique aux symboles et indices utilisés :
    Ar est, pour chaque occurrence, de manière identique ou différente, un groupe aryle ou hétéroaryle comportant 5 à 13 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R ;
    Ar1 est un système de cycle aromatique ou hétéroaromatique comportant 5 à 24 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R et lequel ne contient pas de groupes aryle ou hétéroaryle comportant plus de deux cycles à six éléments condensés directement les uns sur les autres ;
    Y est -C(=O)-N(Ar1)-, -C(=O)-O-, -CR1=CR1-, -CR1=N-, C(R1)2, NR1, O, S, C(=O), C(=S), C(=NR1), C(=C(R1)2), Si(R1)2, BR1, PR1, P(=O)R1, SO ou SO2;
    R, R1 est choisi, pour chaque occurrence, de manière identique ou différente, parmi le groupe constitué par H, D, F, Cl, Br, I, CN, NO2, N(Ar2)2, N(R2)2, C(=O)Ar2, C(=O)R2, P(=O)(Ar2)2, un groupe alkyle, alcoxy ou thioalkyle en chaîne droite comportant 1 à 40 atome(s) de C ou un groupe alkyle, alcoxy ou thioalkyle ramifié ou cyclique comportant 3 à 40 atomes de C ou un groupe alkényle ou alkynyle comportant 2 à 40 atomes de C, dont chacun peut être substitué par un radical ou plusieurs radicaux R2, où un ou plusieurs groupe(s) CH2 non adjacents peut/peuvent être remplacé(s) par R2C=CR2, C≡C, Si(R2)2, C=O, C=S, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S ou CONR2 et où un ou plusieurs atome(s) de H peut/ peuvent être remplacé(s) par D, F, Cl, Br, I, CN ou NO2, un système de cycle aromatique ou hétéroaromatique comportant 5 à 60 atomes de cycle aromatique, lequel peut dans chaque cas être substitué par un radical ou plusieurs radicaux R2, un groupe aryloxy ou hétéroaryloxy comportant 5 à 60 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R2, ou une combinaison de ces systèmes, où deux substituants R adjacents ou plus ou deux substituants R1 adjacents ou plus peuvent en option former un système de cycle aliphatique, aromatique ou hétéroaromatique monocyclique ou polycyclique, lequel peut être substitué par un radical ou plusieurs radicaux R2 et lequel ne contient pas de groupes aryle ou hétéroaryle comportant plus de deux cycles aromatiques à six éléments condensés directement les uns sur les autres ; un radical R sur Ar1 peut en outre également former un système de cycle aliphatique avec un radical R sur Ar ; étant entendu qu'un groupe aryle ou hétéroaryle comportant plus de deux groupes aryle condensés directement les uns sur les autres n'est pas formé par une formation de cycle des radicaux R ou R1 ;
    Ar2 est, pour chaque occurrence, de manière identique ou différente, un système de cycle aromatique ou hétéroaromatique comportant 5-30 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux non aromatiques R2 et lequel ne contient pas de groupes aryle ou hétéroaryle comportant plus de deux cycles aromatiques à six éléments condensés directement les uns sur les autres ; deux radicaux Ar2 qui sont liés au même atome de N ou de P peuvent également être pontés l'un à l'autre ici par une liaison simple ou un pont choisi parmi N(R2), C(R2)2 ou O ;
    R2 est choisi parmi le groupe constitué par H, D, F, CN, un radical hydrocarbone aliphatique comportant 1 à 20 atome(s) de C, un système de cycle aromatique ou hétéroaromatique comportant 5 à 30 atomes de cycle aromatique, où un ou plusieurs atome(s) de H peut/peuvent être remplacé(s) par D, F, Cl, Br, I ou CN, où deux substituants R2 adjacents ou plus peuvent former un système de cycle aliphatique, aromatique ou hétéroaromatique monocyclique ou polycyclique l'un avec l'autre ou les uns avec les autres ;
    n est, pour chaque occurrence, de manière identique ou différente, 0 ou 1, où n = 0 signifie qu'aucun groupe Y n'est présent et en lieu et place, un substituant R est lié ou un hétéroatome du groupe Ar est présent aux positions sur Ar au niveau desquelles Y est lié dans la formule (1) ;
    étant entendu que les radicaux sur Ar ou Ar1 ne contiennent pas un groupe lactame.
  2. Dispositif électronique selon la revendication 1, choisi parmi le groupe constitué par des dispositifs électroluminescents organiques, des circuits intégrés organiques, des transistors à effet de champ organiques, des transistors à film mince organiques, des transistors à émission de lumière organiques, des cellules solaires organiques, des cellules solaires sensibilisées par colorant organiques, des détecteurs optiques organiques, des photorécepteurs organiques, des dispositifs à extinction de champ organiques, des cellules électrochimiques à émission de lumière, des diodes laser organiques (O-laser) et des "dispositifs à émission de plasmon organiques".
  3. Dispositif électronique selon la revendication 1 ou 2, caractérisé en ce que Ar est choisi, de manière identique ou différente pour chaque occurrence, parmi un groupe aryle ou hétéroaryle comportant 6 atomes de cycle aromatique ou un groupe hétéroaryle comportant 5 atomes de cycle aromatique, dont chacun peut être substitué par un radical ou plusieurs radicaux R, où deux substituants R peuvent également former un autre système de cycle l'un avec l'autre.
  4. Dispositif électronique selon une ou plusieurs des revendications 1 à 3, caractérisé en ce que Ar pour n = 0 est choisi parmi les groupes des formules qui suivent (2) à (5) et pour n = 1, est choisi parmi les groupes des formules qui suivent (6) à (8), étant entendu que pour n = 1, au moins un groupe Ar représente un groupe de la formule (6) :
    Figure imgb0498
    Figure imgb0499
     où le lien en pointillés indique la liaison sur le second groupe Ar, # indique la position de la liaison sur Y, * indique la liaison sur l'atome d'azote ou le groupe carbonyle du lactame et en outre :
    X est, de manière identique ou différente pour chaque occurrence, CR ou N ; ou deux groupes adjacents X dans la formule (2) ou la formule (6) représentent un groupe de la formule (9) ou (10) qui suit :
    Figure imgb0500
     dans lesquelles E représente NR, CR2, O ou S, Z représente, de manière identique ou différente pour chaque occurrence, CR ou N et ^ indique les groupes adjacents correspondants X dans la formule (2) ou la formule (6) ;
    V est NR, O ou S.
  5. Dispositif électronique selon une ou plusieurs des revendications 1 à 4, choisi parmi les composés des formules (11) à (21) :
    Figure imgb0501
    Figure imgb0502
    Figure imgb0503
    Figure imgb0504
     où les symboles utilisés présentent les significations données selon les revendications 1 et 4.
  6. Dispositif électronique selon la revendication 4 ou 5, caractérisé en ce que tous les groupes X représentent, de manière identique ou différente pour chaque occurrence, CR.
  7. Dispositif électronique selon une ou plusieurs des revendications 1 à 6, caractérisé en ce que les composés de la formule (1) sont choisis parmi les composés des formules (11b), (11c), (11d), (12b), (12c) et (12d) :
    Figure imgb0505
    Figure imgb0506
     dans lesquelles les symboles utilisés présentent les significations données selon la revendication 1.
  8. Dispositif électronique selon une ou plusieurs des revendications 1 à 7, caractérisé en ce que Ar1 est choisi parmi le groupe constitué par benzène, ortho-, méta- ou para-biphényle, ortho-, méta-, para-terphényle ou terphényle ramifié, quaterphényle linéaire ou ramifié, fluorène, spirobifluorène, carbazole, dibenzothiophène, dibenzofurane, 1,3,5-triazine, pyridine, pyrimidine, indénocarbazole, carbazole ponté ou indolocarbazole ou une combinaison de deux ou trois de ces groupes, où ces groupes peuvent chacun également être substitués par un radical ou plusieurs radicaux R.
  9. Dispositif électronique selon une ou plusieurs des revendications 1 à 8, caractérisé en ce que R est choisi, de manière identique ou différente pour chaque occurrence, parmi le groupe constitué par H, D, F, CN, N(Ar2)2, C(=O)Ar2, un groupe alkyle ou alcoxy en chaîne droite comportant 1 à 10 atome(s) de C ou un groupe alkyle ou alcoxy ramifié ou cyclique comportant 3 à 10 atomes de C ou un groupe alkényle comportant 2 à 10 atomes de C, dont chacun peut être substitué par un radical ou plusieurs radicaux R2, où un ou plusieurs groupes CH2 non adjacents peut/peuvent être remplacé(s) par O et où un ou plusieurs atome(s) de H peut/peuvent être remplacé(s) par D ou F, un système de cycle aromatique ou hétéroaromatique comportant 5 à 30 atomes de cycle aromatique, lequel peut dans chaque cas être substitué par un radical ou plusieurs radicaux R2, ou un groupe aryloxy ou hétéroaryloxy comportant 5 à 30 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R2.
  10. Dispositif électronique selon une ou plusieurs des revendications 1 à 9, lequel est un dispositif électroluminescent organique, caractérisé en ce que le composé de la formule (1) est utilisé en tant que matériau de matrice pour des émetteurs fluorescents ou phosphorescents et/ou dans une couche de blocage de trous et/ou dans une couche de transport d'électrons et/ou dans une couche de blocage d'électrons ou de blocage d'excitons et/ou dans une couche de transport de trous et/ou dans une couche de couplage en sortie optique.
  11. Composé de la formule (1') :
    Figure imgb0507
     dans laquelle ce qui suit s'applique aux symboles et indices utilisés :
    Ar est, pour chaque occurrence, de manière identique ou différente, un groupe aryle ou hétéroaryle comportant 5 à 13 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R ;
    Ar1 est un système de cycle aromatique ou hétéroaromatique comportant 5 à 24 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R et lequel ne contient pas de groupes aryle ou hétéroaryle comportant plus de deux cycles aromatique à six éléments condensés directement les uns sur les autres ;
    Y est -C(=O)-N(Ar1)-, -C(=O)-O-, -CR1=CR1-, -CR1=N-, C(R1)2, NR1, O, S, C(=O), C(=S), C(=NR1), C(=C(R1)2), Si(R1)2, BR1, PR1, P(=O)R1, SO ou SO2;
    R, R1 est choisi, pour chaque occurrence, de manière identique ou différente, parmi le groupe constitué par H, D, F, I, N(Ar2)2, C(=O)Ar2, C(=O)R2, P(=O)(Ar2)2, un groupe alkyle en chaîne droite comportant 1 à 40 atome(s) de C ou un groupe alkyle ramifié ou cyclique comportant 3 à 40 atomes de C ou un groupe alkényle ou alkynyle comportant 2 à 40 atomes de C, dont chacun peut être substitué par un radical ou plusieurs radicaux R2, où un ou plusieurs groupe(s) CH2 non adjacents peut/peuvent être remplacé(s) par R2C=CR2, C≡C, Si(R2)2, C=O, C=S, C=NR2, P(=O)(R2), SO, SO2, S ou CONR2 et où un ou plusieurs atome(s) de H peut/ peuvent être remplacé(s) par D, F, Cl, Br, I, CN ou NO2, un système de cycle aromatique ou hétéroaromatique comportant 5 à 60 atomes de cycle aromatique, lequel peut dans chaque cas être substitué par un radical ou plusieurs radicaux R2, un groupe aryloxy ou hétéroaryloxy comportant 5 à 60 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux R2, ou une combinaison de ces systèmes, où deux substituants R adjacents ou plus ou deux substituants R1 adjacents ou plus peuvent en option former un système de cycle aliphatique, aromatique ou hétéroaromatique monocyclique ou polycyclique, lequel peut être substitué par un radical ou plusieurs radicaux R2; un radical R sur Ar1 peut en outre également former un système de cycle aliphatique avec un radical R sur Ar ; étant entendu qu'un groupe aryle ou hétéroaryle comportant plus de deux groupes aryle condensés directement les uns sur les autres n'est pas formé par formation de cycle des radicaux R ou R1 ;
    Ar2 est, pour chaque occurrence, de manière identique ou différente, un système de cycle aromatique ou hétéroaromatique comportant 5-30 atomes de cycle aromatique, lequel peut être substitué par un radical ou plusieurs radicaux non aromatiques R2 ; deux radicaux Ar2 qui sont liés au même atome de N ou au même atome de P peuvent également être pontés l'un à l'autre ici au moyen d'une liaison simple ou d'un pont choisi parmi N(R2), C(R2)2 ou O ;
    R2 est choisi parmi le groupe constitué par H, D, F, un radical hydrocarbone aliphatique comportant 1 à 20 atome(s) de C, un système de cycle aromatique ou hétéroaromatique comportant 5 à 30 atomes de cycle aromatique, où un ou plusieurs atome(s) de H peut/peuvent être remplacé(s) par D, F, Cl, Br, I ou CN, où deux substituants R3 adjacents ou plus peuvent former un système de cycle aliphatique, aromatique ou hétéroaromatique monocyclique ou polycyclique l'un avec l'autre ou les uns avec les autres ;
    n est, pour chaque occurrence, de manière identique ou différente, 0 ou 1, où n = 1 signifie qu'aucun groupe Y n'est présent et en lieu et place, un substituant R est lié ou un hétéroatome du groupe Ar est présent au niveau des positions sur Ar au niveau desquelles Y est lié dans la formule (1) ;
    étant entendu que les radicaux sur Ar ou Ar1 ne contiennent pas de groupe lactame ;
    les composés qui suivent sont exclus de l'invention :
    Figure imgb0508
    Figure imgb0509
    Figure imgb0510
    Figure imgb0511
  12. Procédé pour la préparation d'un composé de la formule (1'), comprenant :
    a) une formation de liaison entre l'azote d'un lactame et Ar1 ; ou
    b) une formation de liaison entre l'azote d'un amide et Ar ; ou
    c) une formation de liaison entre les deux groupes Ar qui sont liés l'un à l'autre via un groupe amide ; ou
    d) une formation de liaison entre les deux groupes Ar qui sont liés l'un à l'autre via un groupe méthylèneamine, suivie par une oxydation sur le lactame correspondant.
  13. Utilisation d'un composé selon la revendication 11 dans un dispositif électronique, en particulier dans un dispositif électroluminescent organique.
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KR102021162B1 (ko) 2019-09-11
US9337430B2 (en) 2016-05-10
US20140249308A1 (en) 2014-09-04
WO2013064206A1 (fr) 2013-05-10
EP2773721A1 (fr) 2014-09-10
JP2014533435A (ja) 2014-12-11
CN104024371B (zh) 2015-11-25
KR20140097275A (ko) 2014-08-06
CN104024371A (zh) 2014-09-03
JP6239522B2 (ja) 2017-11-29

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